Windy City Romance: The Best Romantic Spots in Chicagoland

by Christopher J.

March 30, 2023


Last fall, Chicago was voted Best Big City in the U.S. for a record sixth consecutive time in the Condé Nast Traveler Readers’ Choice Awards 2022. Everyone acknowledges the city’s world-class architecture, art, parks, sports teams, theatre and entertainment venues, diverse neighborhoods, clubs, hotels and fine dining restaurants. But when you meld all of those together, you combine all of the ingredients for one of the most romantic cities on earth.

If you and your partner visit in summer, you can revel in time spent hiking in the lush green spaces, gardens and parks or along the shoreline on Chicago’s Lakefront Trail, shopping at the Navy Pier, or sailing on Lake Michigan.

If you’re there during the Artic blasts that whirl through the Windy City in winter, you can still spend time hiking, ice skating or walking outdoors. But you can also take advantage of the myriad indoor activities from museums to comedy clubs and countless fabulous restaurants of all cuisines or slide into a thermal bath before retiring to a cozy hotel room to crank up the body heat together.

Here are seven romantic adventures couples can share whether you spend a week or a weekend in Chi-town.

1) Take a Hike, Take Several Hikes Together: You have a wide range of choices. Start with an architectural tour of the city’s famed structural skyline such as Frank Lloyd Wright’s home in Oak Park or The Rookery office building that he designed for Chicago’s Loop downtown to the Chicago Cultural Center, Tribune Tower, and Wrigley Building.

There are abundant wide-open spaces, too,  “Our city doesn’t boast nearby mountains like Seattle or San Francisco, but what the Midwest lacks in elevation it makes up for in natural beauty,” says TimeOut Chicago in its list of 22 Romantic Things to Do in Chicago. “Head to the city’s Northwest Side to go for a walk on the North Branch Trail, head west to trek through the suburbs on the Illinois Prairie Path Trail or cross state lines to visit the gorgeous Indiana Dunes along Lake Michigan.”

2) Take to the Ice: If you would enjoy some fast-paced, puck-based ice action, check out a Chicago Blackhawks Hockey Game. Or if you don’t mind sharing the ice with a few kiddos, TimeOut Chicago says, “dust off your ice skates (or rent a pair onsite) and hit the winding rink at Maggie Daley Park in the heart of downtown Chicago. Hold your honey’s hand as you make your way around the circular path set against skyline views. Don’t forget: you’ll need to plan ahead and make a reservation online if you want to get on the ice.”

3) Take a Bath: Treat yourselves like an ancient Roman or Greek emperor and empress and spend some quality time at the Aire Ancient Baths. Modeled after the ancient tradition of Greek and Roman bathhouses, Aire Ancient Baths provides one of the most distinctive, romantic spa experiences that you can have as a couple. Located in a carefully restored factory from 1902, the original exposed brick and wooden beams transport you into the past. Make sure you take time to explore the choice of baths, icy-cold or steaming hot, and then schedule a couples massage or body treatment and savor the experience with each other.

4) Take in the Legendary Joffrey Ballet: “Ballet showcases the miraculous art of the human body and a night at the ballet, especially one featuring the accomplished Joffrey company, can be most romantic indeed,” writes Jackie Runice, a Chicago local expert, in her article about the most romantic things to do there in USA Today. She labels the Joffrey Ballet “one of the premier dance companies in the world, offers a sensual experience of mystery and artistry” or for a different dance experience, she recommends that you can follow the conga line to Carnivale Chicago for a 1950’s-style show inspired by the original Copacabana Club in New York City. 

5) Take in the Stars at the Forest Preserves District of Cook County: This romantic location tempts with opportunities to stargaze year-round. According to Runice: “In 2021, the International Dark-Sky Association designated the Palos Preserves in southwest Cook County as the largest Urban Night Sky Place in the world. You can see four times more stars there than in the city. Consider Moonlit walks for couples starting from Little Red Schoolhouse Nature Center in Willow Springs.” The Forest Preserves offer year-round and seasonal activities for couples, most for free, featuring more than 70,000 acres with 350 miles of paved and unpaved trails from which to choose.

6) Take Time to Laugh: “A little laughter goes a long way in keeping the playful side of your relationship alive,” claims the Two Drifters blog about 18 romantic things to do in Chicago. Chicago has turned out an impressive number of elite comedians and improv artists from John Belushi and Dan Aykroyd to Steve Carell and Tina Fey, Of course, many got their start training and performing improv at Second City. “Spend an evening laughing with your sweetheart at this iconic Chicagoland comedy club,” says Two Drifters. “Enjoy food and drink while you marvel at gutsy improv performers. This is one of those Chicago date night ideas that is always a winner!” Zanies is another perfect place to find hilarity.

7) Take a Bite, Take a Sip: No need to worry about finding romantic restaurants in Chicago where you can wine and dine your lover any time, any style. “You’ll find dimly lit spots, fondue feasts, rooms with beautiful views and many more intimate options,” boasts TimeOut Chicago. “They all know how to set the mood so that couples can have a lovely and unforgettable experience. The food’s obviously stellar, too, featuring everything from French and Italian cuisine to dry-aged steaks.”

Two other delectable options include Sushi Suite 202 inside the Lincoln Hotel, where you and your partner can immerse yourselves in the warm, highly intimate setting and enjoy a 17-couse, 60-minute omakase sushi dining extravaganza; or the more relaxed and All-Chicago experience of a good, old-fashioned deep-dish pizza at Lou Malnati’s, where you can sample one of their signature cornmeal thin crust pizzas. Mmmmm! *chef’s kiss*

Before retreating to your gorgeous high-rise hotel room, AirBNB in the Chicagoland suburbs, or just your bedroom if you call Chicago home, don’t forget to take a romantic shopping trip at your nearest Lover’s Lane store. You can browse ’til your heart’s content, and a Romance Specialist can help you find exactly what you need to complete your romantic and sexy whirlwind Windy City trip!

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